{"Abbreviation":"4-HA","Aliases":["4-(2-Aminopropyl)phenol","hydroxyamphetamine","Hydroxyamfetamine","Norveritol","Pulsoton","Oxamphetaminium","Oksamfetamin","Oxamfetamin","Paredrinex","Nov-Pholedrin"],"CAS":"103-86-6","ChEBI":"CHEBI:103855","ChEMBL":"CHEMBL1546","ChemicalClasses":["amphetamine"],"Chirality":"racemic","Dosing Info":[],"Drug Indication":"Mydriatic agent (eye pupil dilatation) for diagnosis of ophthalmic nerve lesions.","DrugClasses":[],"EINECS":"203-152-8","European Community (EC) Number":"203-152-8","FDA Pharmacological Classification":"FQR280JW2N","FullSalts":["4-Hydroxyamphetamine hydrobromide"],"HMDB ID":"HMDB0060765","HeavyAtomCount":11,"Human Drugs":"Human drug -\u003e Discontinued","IUPACName":"4-(2-aminopropyl)phenol","InChI":"InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3","InChIKey":"GIKNHHRFLCDOEU-UHFFFAOYSA-N","MeSH Pharmacological Classification":"Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)","MolecularFormula":"C\u003csub\u003e9\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eNO","MolecularWeight":"151.21 g/mol","Opticalactivity":"( + / - )","PrevSalts":["hydrobromide"],"PubChemId":3651,"Record Description":["4-(2-aminopropyl)phenol is a member of amphetamines.","Hydroxyamphetamine is a derivative of amphetamines. Hydroxyamphetamine is intended mainly as local eye drops for diagnostic purposes. It is indirect sympathomimetic agent which cause dilation of the eye pupil before diagnostic test.  Among the minor side effects from its use are: change in color vision, difficulty seeing at night, dry mouth, headache, increased sensitivity of eyes to sunlight, muscle stiffness or tightness and temporary stinging in the eyes. The main use of hydroxyamphetamines as eye drops is the diagnosis of Horner's syndrome which is characterized by nerve lesions.","Hydroxyamphetamine is an Adrenergic Receptor Agonist. The mechanism of action of hydroxyamphetamine is as an Adrenergic Agonist.","4-(2-Aminopropyl)phenol has been reported in Senegalia berlandieri with data available.","Hydroxyamphetamine is an indirect-acting sympathomimetic amine with adrenergic property. Hydroxyamphetamine, when applied topically to the eye, stimulates the release of norepinephrine from postganglionic adrenergic nerves resulting in the stimulation of both alpha and beta adrenergic receptors. Local alpha stimulatory effects include dilation of the pupil, increased flow of aqueous humor, and vasoconstriction; whereas beta stimulatory effects include relaxation of the ciliary muscle and a decreased production in aqueous humor.","HYDROXYAMPHETAMINE is a small molecule drug with a maximum clinical trial phase of IV that was first approved in 1969.","Amphetamine metabolite with sympathomimetic effects. It is sometimes called alpha-methyltyramine, which may also refer to the meta isomer, gepefrine.","4-(2-aminopropyl)phenol is a member of amphetamines."],"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/4-Hydroxyamphetamine","Name":"4-Hydroxyamphetamine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q5955531","Name":"4-Hydroxyamphetamine","Sub":false},{"Link":"https://www.wikidata.org/wiki/Q27268862","Name":"(+)-4-Hydroxyamphetamine","Sub":true}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB09352","Name":"4-Hydroxyamphetamine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/3651","Name":"4-Hydroxyamphetamine","Sub":false},{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/644000","Name":"(+)-4-Hydroxyamphetamine","Sub":true}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1546","Name":"4-Hydroxyamphetamine","Sub":false},{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1927024","Name":"(+)-4-Hydroxyamphetamine","Sub":true}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:103855","Name":"4-Hydroxyamphetamine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=103-86-6","Name":"4-Hydroxyamphetamine","Sub":false},{"Link":"https://commonchemistry.cas.org/detail?cas_rn=1693-66-9","Name":"(+)-4-Hydroxyamphetamine","Sub":true}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0060765","Name":"4-Hydroxyamphetamine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/FQR280JW2N","Name":"4-Hydroxyamphetamine","Sub":false},{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/7UDF5TX27X","Name":"(+)-4-Hydroxyamphetamine","Sub":true}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID3023134","Name":"4-Hydroxyamphetamine","Sub":false},{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID10349250","Name":"(+)-4-Hydroxyamphetamine","Sub":true}]}],"SMILES":"CC(CC1=CC=C(C=C1)O)N","Salts":["hydrobromide"],"SaltsAcidCount":[1],"SaltsAmineCount":[1],"SaltsUNII":["59IG47SZ0E"],"Scheduling":[],"StereoisomerRacemic":"(RS)-4-Hydroxyamphetamine","Stereoisomers":["(+)-4-Hydroxyamphetamine"],"StereoisomersUNII":["7UDF5TX27X"],"StoreUNII":["FQR280JW2N"],"StructureBase64":"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